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| | (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Basic information | | Uses Sources |
| | (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Chemical Properties |
| Melting point | 128-133°C | | Boiling point | 401.9±28.0 °C(Predicted) | | density | 1.080±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 4.68±0.10(Predicted) | | form | Solid | | color | White to Off-White | | Optical Rotation | -6.5461°(C=1.0048g/100ml DMF) | | Major Application | pharmaceutical small molecule | | InChI | InChI=1S/C9H17NO3/c1-6(2)3-7(4-8(10)11)5-9(12)13/h6-7H,3-5H2,1-2H3,(H2,10,11)(H,12,13)/t7-/m1/s1 | | InChIKey | NPDKTSLVWGFPQG-SSDOTTSWSA-N | | SMILES | C(O)(=O)C[C@@H](CC(N)=O)CC(C)C | | CAS DataBase Reference | 181289-33-8(CAS DataBase Reference) |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Skin Irrit. 2 |
| | (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Usage And Synthesis |
| Uses | (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid is a useful chemical intermediate for manufacturing of the anticonvulsant drug, Pregabalin1, 2.
| | Sources |
- https://quod.lib.umich.edu/a/ark/5550190.0011.a22?rgn=main;view=fulltext
- https://www.researchgate.net/publication/269660675_Synthesis_and_characterization_of_impurities_of_an_anticonvulsant_drug_Pregabalin
| | Chemical Properties | White Solid | | Uses | An Impurity of the anti-convulsant (S)-Pregabalin (P704790). | | Synthesis | The general procedure for the synthesis of (R)-(-)-3-(aminocarbonylmethyl)-5-methylhexanoic acid from the compound (CAS:1385049-51-3) is as follows:
Example 10f1: Synthesis of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid
1. ammonia (116 ml) was added to the diastereomeric salt (14.5 g) and the mixture was heated to 80 °C at room temperature.
2. After maintaining the reaction at this temperature for 5 hours, the reaction mixture was cooled to room temperature.
3. The reaction mixture was extracted using dichloromethane (5 x 50 ml).
4. The aqueous layer was cooled to 0 °C and acidified to pH 1 with concentrated hydrochloric acid.
5. The acidified aqueous layer was extracted using hot ethyl acetate (5 x 50 ml).
6. All organic extracts were combined and concentrated under reduced pressure to give enantiomerically enriched amide I as a white solid.
Yield: 8 g, 53% yield; HPLC purity: 99.39%. | | References | [1] Patent: WO2012/93411, 2012, A2. Location in patent: Page/Page column 23 |
| | (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Preparation Products And Raw materials |
| Raw materials | Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3S)--->3-Carbamoymethyl-5-methylhexanoic acid-->(3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid-->Hexanoic acid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3R)-, compd. with (βR)-β-aminobenzeneethanol (1:1)-->Hexanoic acid, 5-methyl-3-[2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]-, (3R)--->Hexanoic acid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3R)-, compd. with α-ethylbenzenemethanamine (1:1)-->Ammonia-->Hydrochloric acid |
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